"At least another 6 months before we can finish the project," I offered. As the CTO of startup that grew to be sold for several hundred million, taking months to deliver a key revenue-driver wasn't acceptable.
What also wasn't acceptable was hiring remote employees. The usual mantra of having people in-house for collaboration & communication blocked progress. This eventually improved, years before COVID-19 forced the issue.
There's truth to The Mythical Man-Month, but a small team still has a finite cap. With a high-visibility project potentially impacting the next two quarters, I got the go-ahead to pilot hiring remote engineers.
Even with blasting the Houston job opening across all known channels, I was lucky to get an application a week.
Yes, there was the usual noise problem of applicants who did not read the description or have the required experience, but now I could focus on the right hire versus hiring out of desperation.
Being the first remote hire, I deferred to the candidates on why this remote role was a great for both parties. The key benefits that consistently surfaced were:
Family. The most exciting opportunities could not compete with losing proximity to family. This was especially true for people who were caretakers, or recently had children.
Productivity. Well-adjusted remote employees had a routine focused on entering focus-mode, devoid of in-office distractions.
Even still, they conceded obvious drawbacks:
Communication. Both sides have to make a conscious effort to bridge the physical divide. Too often the expectation is that the remote employee over-communicates, but the minority is always at a disadvantage.
Culture. Culture is the byproduct of a collective, social group. Being remote and in the minority compared to a pre-existing, in-office team makes acclimating and changing culture difficult.
My responsibility was to hire for the benefits, while mitigating these risks.
(Name and pronouns have been changed.)
Taylor had prior experience working remotely, and had the crucial trait of desire to help others. This meant we could discuss the state of affairs, what was needed & why, then put them on auto-pilot.
Changing jobs is stressful enough already. Even changing insurance in the U.S. is non-trivial and risky. So much of the experience is outside of the new hire's control. To counter this, I made sure that new hires got to hand-pick and customize their new machines. Delivered to their home like an early Christmas present, they regained a sense of trust, responsibility, and ownership that doesn't come across from a re-gifted, 5-year old laptop from accounting.
With hardware out of the way, re-establishing the team's culture was next.
Within the first few weeks of work, Taylor flew into Houston to meet the team. Prior to this, there were only phone calls! (Not everyone is capable of travel, but I've found it creates a connection that only in-person, human interactions can.)
Everyone got along great, and what was a closed-circle widened to an arc to be more inclusive. After a few days of establishing a rapport and setting up project milestones, Taylor headed back home.
I thought we were off to a perfect start.
During a 1-on-1 following our in-person meeting with Taylor, they dropped a bombshell.
I felt like an outsider.
I was floored. How did we mess up so badly, so quickly!?
With only an in-office presence, we had our own unique culture. We normalized our daily happy hours, had implicit expectations to attend, and excused off-color remarks that had good intentions.
Sure, we're flawed humans, but our "culture" hadn't been previously challenged.
Taylor went along for their own self-preservation and appearances, but was uncomfortable nonetheless. (Diversity has a way of exposing systemic flaws.)
Embarrassed and apologetically, we got into the details and, most importantly, what coming out of the other side of this would look like.
This already meant re-establishing trust: that Taylor wouldn't be seen or treated as an outsider, that the team's behavior wouldn't be exclusionary, and that we were honest with each other. Being critical, even when it is the right thing to do, is a huge risk to the whistle-blower, even when in secret.
This wasn't the first time what we considered "culture" was challenged. Pain has a way of telling us something's wrong.
But even with the team's improvements to an evolving culture, feeling like an outsider wasn't solved.
Hallway conversations are often celebrated as a benefit of in-office teams. (Shoulder tapping, its nefarious cousin is hardly mentioned.)
These were noticeably absent to Taylor, even with Slack. It was all too easy for two people sitting across from each other to just have a conversation.
Did my decree to "put more communication in Slack" help? No.
Did my effort to convert more conversations into meetings help? God no.
The secret to improving communication? Send the team home.
I tried improving communication in the office to no avail, but sending the in-office team to work remotely created the empathy and friction necessary to level the playing field for the entire team.
Yes, more communication ended up in Slack & emails, but out of necessity. Shoulder-tapping dropped because sometimes a few minutes of struggling with a problem alone without bothering someone else is all that's needed to get unblocked.
Unexpectedly, with the entire team spending a few days a week working remotely, the same benefits touted during the interview stage started bubbling up in 1-on-1s for the entire team.
The hour commute each way wasn't missed. Dads were picking up daughters from school for the first time. The team was happy. And productivity didn't suffer. What started as 2 days a week grew to 3, then eventually parts of the team were coming in to the office when remote workers were.
It wasn't long before the team doubled in size. Other teams began hiring remotely, too, even to the point of eclipsing the number of in-office workers.
And the numbers shared in the following board meetings were evidence of remote's success: that 6-month out project got cut in half (thanks to additional bandwidth and reducing randomization of tasks), with a 13% bump to the conversion funnel to boot. (Spoiler: performance matters)
Remote became the default.